{{Short description|Psychedelic drug}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Infobox drug | drug_name = | image = Methylpropyltryptamine.svg | image_class = skin-invert-image | width = 225px | image2 = MPT 3D.png | image_class2 = bg-transparent | width2 = 225px
<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = Oral<ref name="TiHKAL" /> | class = Serotonergic psychedelic; Hallucinogen | ATC_prefix = None | ATC_suffix =
<!-- Legal status --> | legal_status =
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | CAS_number_Ref = {{Cascite|correct|CAS}} | CAS_number = 850032-72-3 | CAS_supplemental = | PubChem = 74405270 | PubChemSubstance = | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 96351249 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = CWD3LY2N3Z | KEGG = | ChEBI = | ChEMBL = | NIAID_ChemDB = | PDB_ligand = | synonyms = MPT; ''N''-Methyl-''N''-propyltryptamine
<!-- Chemical data --> | IUPAC_name = ''N''-[2-(1''H''-indol-3-yl)ethyl]-''N''-methylpropan-1-amine | C=14 | H=20 | N=2 | SMILES = CCCN(C)CCC1=CNC2=C1C=CC=C2 | StdInChI = 1S/C14H20N2/c1-3-9-16(2)10-8-12-11-15-14-7-5-4-6-13(12)14/h4-7,11,15H,3,8-10H2,1-2H3 | StdInChIKey = SZUNESAKJQIJAC-UHFFFAOYSA-N }}
'''Methylpropyltryptamine''' ('''MPT'''), also known as '''''N''-methyl-''N''-propyltryptamine''', is a psychedelic drug of the tryptamine family. It is a homologue of methylethyltryptamine (MET).<ref name="TiHKAL" />
==Use and effects== In his book ''TiHKAL'' (''Tryptamines I Have Known and Loved''), Alexander Shulgin described MPT's effects as being unknown and its dose as being greater than 50{{nbsp}}mg orally.<ref name="TiHKAL">{{CiteTiHKAL }}</ref>
==Interactions== {{See also|Psychedelic drug#Interactions|Trip killer#Serotonergic psychedelic antidotes}}
==Chemistry== ===Detection=== An analytical method for MPT's detection has been reported.<ref>{{cite journal | vauthors = Brandt SD, Freeman S, Fleet IA, Alder JF | title = Analytical chemistry of synthetic routes to psychoactive tryptamines. Part III. Characterisation of the Speeter and Anthony route to N,N-dialkylated tryptamines using CI-IT-MS-MS | journal = The Analyst | volume = 130 | issue = 9 | pages = 1258–1262 | date = September 2005 | pmid = 16096671 | doi = 10.1039/b504001a | bibcode = 2005Ana...130.1258B }}</ref>
===Crystal structure=== In 2019, Chadeayne et al. published the crystal structure of MPT.<ref>{{Cite journal | vauthors = Chadeayne AR, Golen JA, Manke DR | title = N -Methyl- N -propyltryptamine (MPT) | journal = IUCrData | volume = 4 | issue = 7 | article-number = x190962 | date = 2019-07-28 | doi = 10.1107/S2414314619009623 | url = http://scripts.iucr.org/cgi-bin/paper?S2414314619009623 | issn = 2414-3146 | doi-access = free | bibcode = 2019IUCrD...490962C }}</ref> The authors describe the structure as "...a single molecule in the asymmetric unit, with an indole group that demonstrates a mean deviation from planarity of 0.015 A°."
===Analogues=== Analogues of MPT include 4-HO-MPT, 5-MeO-MPT, methylethyltryptamine (MET), ethylpropyltryptamine (EPT), ethylisopropyltryptamine (EiPT), and dipropyltryptamine (DPT), among others.<ref name="TiHKAL" />
==Society and culture== ===Legal status=== ====Canada==== MPT is not a controlled substance in Canada as of 2025.<ref name="CDSA">{{cite web | title=Controlled Drugs and Substances Act | website=Department of Justice Canada | url=https://laws-lois.justice.gc.ca/eng/acts/c-38.8/FullText.html | access-date=19 January 2026}}</ref>
====United States==== MPT is not an explicitly controlled substance in the United States.<ref name="OrangeBook2026">{{citation | title = Orange Book: List of Controlled Substances and Regulated Chemicals (January 2026) | date = January 2026 | publisher = U.S. Department of Justice: Drug Enforcement Administration (DEA): Diversion Control Division | location = United States | url = https://www.deadiversion.usdoj.gov/schedules/orangebook/orangebook.pdf}}</ref> However, it is an isomer of diethyltryptamine (DET), which is a schedule I controlled substance in this country, and so may be considered a controlled substance in the United States similarly.<ref name="OrangeBook2026" /><ref name="DEA2007">{{cite web | author=Drug Enforcement Administration | title=Definition of “Positional Isomer” as It Pertains to the Control of Schedule I Controlled Substances | website=Federal Register | date=3 December 2007 | url=https://www.federalregister.gov/documents/2007/12/03/E7-23413/definition-of-positional-isomer-as-it-pertains-to-the-control-of-schedule-i-controlled-substances}}</ref>
==See also== * Substituted tryptamine
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5175 MPT - Isomer Design] * [https://psychonautwiki.org/wiki/MPT MPT - PsychonautWiki] * [https://www.bluelight.org/xf/threads/399129 The Big & Dandy MPT Thread - Bluelight]
{{Psychedelics}} {{Tryptamines}}
Category:N,N-Dialkyltryptamines Category:Methyl compounds Category:Propyl compounds Category:Psychedelic tryptamines Category:Tertiary amines